An on-line service manages downloads of purchased digital content. Information regarding the digital content items that are purchased by each user and the terms of use of those purchased items is maintained. Information regarding the formats of digital content items that each device is adapted to receive is maintained. Upon determining that a user wishes to download a digital content item, the requested digital content is downloaded in an appropriate format for a particular digital device provided the recorded information indicates the content item has been purchased by the user and the download is within the quantity of downloads authorized by the terms of the purchase.